In September 2020, Katie Holmes and then-boyfriend Emilio Vitolo Jr. were frequently photographed navigating the streets of New York City, establishing a blueprint for transitional autumn style.
Their eight-month relationship, which concluded in May 2021, was often defined by these coordinated, low-key walks through Manhattan. During a stroll on September 22, the pair showcased how to balance classic tailoring with city-ready footwear.
Emilio Vitolo Jr. and Katie Holmes step out hand-in-hand in New York City on September 22, 2020, with Holmes pairing a structured navy peacoat and straight-leg jeans with classic black Gucci horsebit loafers—an effortless blend of polished tailoring and relaxed, city-ready ease (Credit: Instar / WENN)
The duo opted for classic fall staples, with the chef looking dapper in a long charcoal-gray coat over a gray polo shirt and black jeans.
He accessorized with a checked flat cap, a white face mask, and a pair of black lace-up ankle boots.
Chef Emilio Vitolo Jr. looks dapper in a long charcoal gray coat and a flat cap
Known for her classic cool-girl style, Katie kicked off autumn in a long, navy blue double-breasted peacoat with gold buttons.
Underneath her fall staple, the American actress wore a fitted black ribbed top. She then paired the look with straight-leg denim jeans that feature a high waist and a relaxed fit.
Katie Holmes welcomes fall in a navy blue peacoat and straight-leg denim jeans
The mom-of-one kept things simple by skipping elaborate jewelry, except for a tiny pair of hoop earrings. In an attempt to avoid drawing attention, Katie accessorized with oversized cat-eye sunglasses along with a disposable face mask.
She then carried a Sharkchaser Bubble Notte bucket bag over her shoulder and wore her hair in a messy bun.
Katie Holmes effortlessly styles her hair in a messy bun and keeps a low-key look with large sunglasses
A pair of Gucci “Jordaan” loafers finished off Katie Holmes’ chic fall ensemble, anchoring her look with the sleek, fashion-forward silhouette that sets this style apart from the house’s more traditional horsebit designs.
Introduced under Alessandro Michele, the Jordaan refines Gucci’s iconic loafer with an elongated almond toe and a slimmer profile—more polished than the heritage 1953 model and more structured than the foldable Brixton.
Katie Holmes grounds her fall look with black Gucci Jordaan horsebit loafers, the slim leather silhouette and signature gold hardware adding a polished finish to her relaxed straight-leg denim
Crafted in supple leather using Blake construction for flexibility and a lightweight feel, the Jordaan is designed for effortless, all-day wear, with its low 0.5-inch heel and streamlined shape making it a natural fit for city dressing.
The signature gold-tone horsebit—sleeker and more delicate than earlier iterations—adds just enough polish to elevate denim without sacrificing ease, striking that precise balance between tailored and relaxed that defines Holmes’ off-duty style.
Why Katie Holmes’ Gucci Loafers Still Define Polished Off-Duty Style
Katie Holmes’ New York look proves why Gucci loafers remain a quiet-luxury essential: they ground denim and tailoring with the ease of a flat, while the house’s signature horsebit hardware keeps the finish unmistakably refined.
For more celebrity styling inspiration, these Gucci loafer moments show how the classic silhouette moves from street style to red-carpet dressing.
👞 Explore Gucci Loafer Style Stories:
- 🖤 Emma Roberts’ Gucci Horsebit loafers show how the 1953 classic can sharpen cropped denim and an easy off-duty outfit with polished, androgynous ease.
- 🌆 Katie Holmes’ go-to Gucci Jordaan loafers make a strong case for the horsebit loafer as an everyday city staple, styled with denim, simple layers, and understated New York polish.
- 👖 Gigi Hadid’s NYFW Gucci lug-sole loafers bring a tougher model-off-duty edge to cargo denim, baggy jeans, and Fashion Week street style.
- 💚 Kirsten Dunst’s black Gucci Jordaan loafers soften Milan Fashion Week dressing with a comfortable, refined finish beneath wide-leg denim and a tailored wool coat.
- 🔥 A$AP Rocky’s Gucci Princetown fur-lined loafers turn the house’s horsebit signature into a bold red-carpet statement, proving the loafer can be as daring as it is classic.
- 📘 This guide to the best loafer brands places Gucci’s Horsebit loafer at the center of modern luxury footwear, from classic leather styles to Jordaan and Princetown variations.
First hitting the shelves in the 1950s, this black apron-toe leather loafer, polished with a goldtone horsebit, pairs well with both casual and more polished outfits